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Unlike all other synthetic methods, this approach utilized epoxide ring\u2010opening reactions to form two C\u2212N bonds and is characterized by the absence of redox reactions. Mugineic acid was synthesized from three readily available fragments on a gram scale in 6 steps. The protected 2\u2019\u2010hydroxynicotianamine was also synthesized in 4 steps, and the dansyl group, serving as a fluorophore, was introduced through a click reaction after propargylation of the 2\u2019\u2010hydroxy group. The dansyl\u2010labeled nicotianamine (NA) iron complexes were internalized by oocytes overexpressing ZmYS1 (from maize) or PAT1 (from human) transporters, indicating successful transport of the synthesized NA\u2010probe through these transporters.<\/jats:p>","DOI":"10.1002\/anie.202401411","type":"journal-article","created":{"date-parts":[[2024,3,19]],"date-time":"2024-03-19T07:30:16Z","timestamp":1710833416000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Epoxide Ring\u2010Opening Reactions for Abundant Production of Mugineic Acids and Nicotianamine Probes"],"prefix":"10.1002","volume":"63","author":[{"given":"Kimika","family":"Kayano","sequence":"first","affiliation":[{"name":"Pharmaceutical Sciences Tokushima University  1-78-1 Shomachi Tokushima 770-8505 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tomohiro","family":"Tsutsumi","sequence":"additional","affiliation":[{"name":"Pharmaceutical Sciences Tokushima University  1-78-1 Shomachi Tokushima 770-8505 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1891-2609","authenticated-orcid":false,"given":"Yoshiko","family":"Murata","sequence":"additional","affiliation":[{"name":"Bioorganic Research Institute Suntory Foundation for Life Sciences  8-1-1 Seikadai, Seika-cho, Soraku-gun Kyoto 619-0284 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Chie","family":"Ogasa","sequence":"additional","affiliation":[{"name":"Pharmaceutical Sciences Tokushima University  1-78-1 Shomachi Tokushima 770-8505 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Takehiro","family":"Watanabe","sequence":"additional","affiliation":[{"name":"Bioorganic Research Institute Suntory Foundation for Life Sciences  8-1-1 Seikadai, Seika-cho, Soraku-gun Kyoto 619-0284 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ryota","family":"Sato","sequence":"additional","affiliation":[{"name":"Pharmaceutical Sciences Tokushima University  1-78-1 Shomachi Tokushima 770-8505 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0151-5893","authenticated-orcid":false,"given":"Sangita","family":"Karanjit","sequence":"additional","affiliation":[{"name":"Pharmaceutical Sciences Tokushima University  1-78-1 Shomachi Tokushima 770-8505 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1548-5656","authenticated-orcid":false,"given":"Kosuke","family":"Namba","sequence":"additional","affiliation":[{"name":"Pharmaceutical Sciences Tokushima University  1-78-1 Shomachi Tokushima 770-8505 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2024,4,9]]},"reference":[{"key":"e_1_2_3_1_1","unstructured":"\u00a0"},{"key":"e_1_2_3_2_2","first-page":"819","volume":"75","author":"Wallace A.","year":"1960","journal-title":"Proc. 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The NMR yield was calculated by subtracting the amount of ethyl acetate based on the1H NMR integral ratio."},{"key":"e_1_2_3_50_1","unstructured":"The direct tosylation reaction of aluminum alkoxide resulting from the epoxide ring-opening reaction did not proceed. The other leaving groups methanesulfonyl chloride and chloromethyl sulfonyl chloride could not be selectively introduced into the primary alcohol leading to the formation of bis-sulfonylated products. This suggested that the reactivity of the two alcohols is equivalent. In addition conversion of the primary alcohol to halides by the Appel reaction or the formation of the cyclic sulfonyl ester resulted in a complex mixture."},{"key":"e_1_2_3_51_1","unstructured":"The direct conversion of the diol9to the epoxide11was unsuccessful due to difficulties in selectively activating the primary alcohol. In addition one-pot epoxide formation from the tosylation reaction of9was also difficult because of the need for strict control of equivalent KOH."},{"key":"e_1_2_3_52_1","doi-asserted-by":"publisher","DOI":"10.1246\/cl.230166"},{"key":"e_1_2_3_53_1","doi-asserted-by":"publisher","DOI":"10.1093\/oxfordjournals.jbchem.a124432"},{"key":"e_1_2_3_54_1","unstructured":"Attempts were made to detect the aziridine18\u2009Ain the reaction mixture but no spectral evidence for the formation of18\u2009Awas obtained. On the other hand when18(Rf=0.53 hexane\/AcOEt=1\/1) was simply stirred iniPrOH new TLC spots appeared and one spot (Rf=0.23 hexane\/AcOEt=1\/1) showed a molecular weight consistent with aziridine18\u2009Aby TLC-MS analysis. However no further confirmation was obtained. 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